Boston · FOOD & DRINK

The 15 Food & Drink Experiences in Boston Worth Booking Ahead

39 tours  ·  from $34 a head

The better food & drink experiences book up early in summer and again in October. Below: the 15 to reserve first, what each includes and how they differ.

Boston Food & History: Pizza, North End & Freedom Trail - Old City Hall, King’s Chapel and Granary Burying Ground
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Boston Food & History: Pizza, North End & Freedom Trail

1.Boston Food & History: Pizza, North End & Freedom Trail

★★★★★★★★★★5.0 · 1,772 reviews · 5 hours (approx.) · from $90Our pick

Spend about five hours walking from Boston Harbor through the North End and along the Freedom Trail, with bread, pizza, an Italian deli sandwich, coffee and other treats along the way. Guides such as Nabil, Bob, Lexie and Claire have led lively history walks for groups of up to 12. Expect about five miles on foot.

“Nabil was an outstanding g your guide - funny, knowledgeable and super friendly. Will def do another tour in the future.”

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Boston North End Food Tour of 6+ Tastings, Cannoli, Lobster Roll - Hanover Street: food street, city street
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Boston North End Food Tour of 6+ Tastings, Cannoli, Lobster Roll

2.Boston North End Food Tour of 6+ Tastings, Cannoli, Lobster Roll

★★★★★★★★★★5.0 · 1,404 reviews · 3 hours 30 minutes (approx.) · from $119

Spend about three hours walking from the New England Holocaust Memorial toward Boston’s North End, tasting New England seafood and Italian favorites with a local guide. Expect a group of no more than 12, stories along Hanover Street, and a final secret dish. The menu and stops can change, so come hungry and wear comfortable shoes.

“Perfect portions A nice mix of tastings Just enough walking between locations to give you a breather”

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Boston’s North End Food Tour: Italian Flavors & Heritage Walk - Old North Church and Paul Revere’s Story
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Boston’s North End Food Tour: Italian Flavors & Heritage Walk

3.Boston’s North End Food Tour: Italian Flavors & Heritage Walk

★★★★★★★★★★5.0 · 1,322 reviews · 2 hours (approx.) · from $70

Walk about 1.3 miles through the North End with a local guide, stopping for fresh bread, Italian meats and cheeses, pizza, pastry, and coffee. The group is capped at 12, and the route includes the Old North Church when available. Guides such as Lexie, Nabil, Bob, and Claire have led the tour.

“This tour was off the charts. Definitely the best food walking tour I've been on. Nabil was so knowledgeable, funny, and really present with each of us. He obviously loves what he does. We all felt so special as he guided us straight to hidden gems we NEVER would have found on our own, where the owners and workers behind the counters all knew him and greeted us all warmly. He knew tons of history and loved discussing things with us. The food we sampled was yummy, authentic, made with love, and DELICIOUS! Definitely filling too! Best tour!!”

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Boston Pizza Lovers Food and History Walking Food Tour - Copp’s Hill and the view toward Charlestown
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Boston Pizza Lovers Food and History Walking Food Tour

4.Boston Pizza Lovers Food and History Walking Food Tour

★★★★★★★★★★4.5 · 1,082 reviews · 2 hours 50 minutes (approx.) · from $69

Walk Boston’s North End with a local guide, stopping for three full-size pizza slices and a cannoli from Modern Pastry. Along the way, hear stories about Paul Revere, Old North Church, Copp’s Hill, and the Revolution. Guides such as Scotty and Big Al have led the tour, though your guide may vary.

“This was a terrific tour! Scotty, our tour guide, was knowledgable, funny, and informative, and gave us great ideas for things to do and see after our tour -- and where to find a great steak! The pizza was delicious -- it's amazing to be able to link the food to the Freedom Trail. Would highly recommend this tour!”

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Newport Neighborhood Food Tour - Historic Newport in short, useful pauses
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Newport Neighborhood Food Tour

5.Newport Neighborhood Food Tour

★★★★★★★★★★5.0 · 597 reviews · 3 hours 15 minutes (approx.) · from $99

Spend about three hours and 15 minutes walking Newport with a local guide, tasting dishes at neighborhood eateries and hearing stories about the city’s architecture and past. The route can include a Jamaican patty, seasonal bites at Stoneacre Brasserie and Mexican-inspired food at Perro Salado. Guides such as Angel, Erin, Jack and Lesli have led tours. Optional alcoholic tastings cost extra.

“As an RI native, I still learned a lot about the history of Newport and many food options I wasn't aware of. Delicious and such a great day!”

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Boston's North End Food and History Walking Tour - From Sicilian pizza to the Italian market
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Boston’s North End Food and History Walking Tour

6.Boston’s North End Food and History Walking Tour

★★★★★★★★★★5.0 · 459 reviews · 3 hours (approx.)

Spend about three hours walking Boston’s North End with a local guide, often Paula, who connects the neighborhood’s Italian roots with its food. Expect tastings at family-run shops, a sit-down lunch with wine, and treats such as cannoli, gelato, and espresso. The group is capped at 10, and the tour returns to its starting point.

“The tour was excellent. We were introduced to various Italian specialties based on the area of Italy where they came from. The tour guide was very knowledgeable of the history of the North End and gave us interesting information to help us understand its origins.”

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Boston’s Politically Incorrect North End Food Tour - The meal is part of the route
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Boston’s Politically Incorrect North End Food Tour

7.Boston’s Politically Incorrect North End Food Tour

★★★★★★★★★★5.0 · 453 reviews · 3 hours (approx.) · from $98

Join Anthony, a North End native also known as Flash, for a three-hour walking tour through Boston’s Little Italy. Visit five to seven local eateries for generous samples such as an Italian sub, ravioli, pizza or arancini, and dessert, while hearing neighborhood history and stories about an alleged mob house. Expect blunt humor and plenty of walking.

“Wonderful time! Great way to see hidden gems you wouldn’t be able to find on your own. Anthony is a legend around North End and is very kind. Just a warning though he will show up a bit late! It’s just his thing lol great experience! 10/10”

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Newport Walking Food And History Tour - Starting at the Wave Sculpture
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Newport Walking Food And History Tour

8.Newport Walking Food And History Tour

★★★★★★★★★★5.0 · 377 reviews · 2 hours 30 minutes to 3 hours (approx.) · from $123

Walk 1.5 miles through Newport with a guide such as Tom, Sue, or Susan, stopping for five food and drink tastings along the way. You’ll hear about the city’s 300-year history, see Brown and Howard Wharf and the Elms Mansion gardens, and finish near the center of town at O’Brien’s Pub.

“The guide was fantastic. The quantity of food was more than samples. Sit down restaurants gave us meals. So much excellent food! You won’t be disappointed.”

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Boston: North End & Little Italy Food Tour with Local Dishes - Following Freedom Trail stories into Little Italy
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Boston: North End & Little Italy Food Tour with Local Dishes

9.North End & Little Italy Food Tour with Local Dishes

★★★★★★★★★★4.8 · 229 reviews · 2 - 3 hours · from $60

Choose a two-hour express walk or a three-hour food tour from Quincy Market toward the North End, pairing clam chowder and local specialties with Freedom Trail stories. Guides such as Sean, Evan, and Jack have led the route, but guide assignments vary. The longer option adds seafood tastings and more neighborhood time.

“We loved the tour. The food choices were a great selection. I loved how everywhere we went they were expecting us so it made it easy. Our tour guide Kyle was very knowledgeable and easy-going. I would definitely recommend this.”

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Boston Seafood Lovers Food and History Walking Tour - Oysters and shrimp at Long Wharf
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Boston Seafood Lovers Food and History Walking Tour

10.Boston Seafood Lovers Food and History Walking Tour

★★★★★★★★★★5.0 · 208 reviews · 2 hours 45 minutes (approx.) · from $159

Walk from Boston’s North End to the waterfront and Faneuil Hall, stopping for clam chowder, oysters, shrimp, a full lobster roll and cannoli. A guide such as Dan or Big Al mixes local food with stories of Paul Revere, the Old State House and Boston’s old port. Expect about 2 hours 45 minutes on foot, with a small group of up to 12.

“Dan was so great! I really enjoyed his sense of humor and his knowledge of the best restaurants in Boston. I had the best clam chowder of my life!”

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North End to Freedom Trail: Boston’s Food & History - Follow the Revolution through Boston’s streets
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North End to Freedom Trail: Boston’s Food & History

11.North End to Freedom Trail: Boston’s Food & History

★★★★★★★★★★4.8 · 185 reviews · from $99

Start beside the Greenway Carousel for a five-hour, five-mile walk through the North End and along the Freedom Trail. Sample local Italian food, visit historic sites including Old North Church or an alternative, and finish near the Boston Public Garden. Groups are capped at 12, and guides such as Bob, Conor, and Lexie have led the tour.

“Our guide, Lucy, was very informational and entertaining to listen too. The food was great and would suggest this tour to people who want to see more of the north end and the historic sites. Make sure not to eat breakfast before going, lots of food along the way!”

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Boston Food of the North End Private Walking Tour - Finding the stories behind the storefronts
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Boston Food of the North End Private Walking Tour

12.Boston Food of the North End Private Walking Tour

★★★★★★★★★★5.0 · 174 reviews · from $147

Walk from the Greenway into Boston’s North End with an English-speaking guide, sampling foods such as bread, pastry, pizza, or meat and cheese, plus a café drink. The two-hour private tour also covers Paul Revere Mall and includes admission to Old North Church when it is open. Food stops vary by day, and guides have included Tyler, Nabil, and Maz.

“The trip was outstanding. Great food and really good insights on the local history. Our guide was very knowledgeable and introduced us to great local restaurants.”

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Boston Private Food Tour of 6+ Tastings, Cannoli, Lobster Roll - A North End plaque with a difficult story
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Boston Private Food Tour of 6+ Tastings, Cannoli, Lobster Roll

13.Boston Private Food Tour of 6+ Tastings, Cannoli, Lobster Roll

★★★★★★★★★★5.0 · 165 reviews · 3 hours (approx.) · from $395

Spend about three hours with your private group tasting New England and Italian favorites, from clam chowder and a lobster roll to brick-oven pizza and mini cannoli. The walk starts at the New England Holocaust Memorial, visits Boston Public Market and North End landmarks, and ends on Hanover Street. Guides have included Kyle, Ampora, and Elaun.

“Elaun was prompt and knowledgeable during our Boston food tour. He provided us with history and facts along the way. We enjoyed all of the food options and would definitely do this again! Elaun was even able to accommodate dietary restrictions. Thank you Elaun for a memorable day in Boston!”

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Boston: Food and History of The Freedom Trail Private Tour - Eating your way through the North End
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Boston: Food and History of The Freedom Trail Private Tour

14.Food and History of The Freedom Trail Private Tour

★★★★★★★★★★5.0 · 159 reviews · from $269

Set out at 10 a.m. from the Greenway for a private, five-hour walk through Faneuil Hall, the North End, and key Freedom Trail sites. Your English-speaking guide serves food samples that add up to a meal, plus a local drink and a Boston treat. Guides have included Alex, Mark, Sully, and Molly; the route ends in the Public Garden.

“Perfect summary of the major events in Boston and a visit to the good restaurants in the Italian district. We enjoyed our tour very much.”

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North End Boston Food Tour - What the $98 price means
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North End Boston Food Tour

15.North End Boston Food Tour

★★★★★★★★★★5.0 · 147 reviews · 2 to 3 hours (approx.) · from $98

Spend about three hours walking Boston’s North End with lifelong local guide Bobby Agrippino. You’ll hear stories of the neighborhood’s immigrant roots and traditions, visit mom-and-pop shops, and sample Italian food with wine and limoncello pairings. The tour starts at the Tony DeMarco Statue and ends near Mike’s Pastry.

“Bobby provides a great tour that gives historical information and first hand accounts of the neighborhood's past. The food and beverage stops are good enough, but the history behind each make for a greater experience.”

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New in Food & Drink

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★ 5.0Dumplings to Dim Sum: Food and History Tour of Boston’s ChinatownFrom $13515 reviews
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★ 4.5Iconic Food Tasting & History Tour – DowntownFrom $12512 reviews
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